(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 1027961-34-7
• Molecular Formula: C₂₄H₂₈INO₆
• Molecular Weight: 553.394
• Mol file: 1027961-34-7.mol

Synonyms:(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

There total 1 articles about (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate (704910-33-8) → (2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (1027961-34-7)

Guidance literature:

methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate; With titanium(IV) isopropylate; cyclopentylmagnesium chloride; In diethyl ether; at -40 ℃; for 1h;

With iodine; In tetrahydrofuran; diethyl ether; at -40 - 23 ℃; for 4h;

DOI:10.1021/ol0508734

Reference yield:

(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (1027961-34-7) → methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde (704910-34-9)

Guidance literature:

With triethylamine; In dichloromethane; at 23 ℃; for 0.5h;

DOI:10.1021/ol0508734

Reference yield:

(2R,3S)-2-Benzyloxymethyl-3-hydroxy-4-iodomethyl-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (1027961-34-7) → (2R,3S,4R)-3-Hydroxy-4-(2-hydroxy-ethyl)-2-[(S)-1-(isopropyl-dimethyl-silanyloxy)-2-methyl-propyl]-1-(4-methoxy-benzyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (857681-76-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 3.53 g / triethylamine / CH₂Cl₂ / 0.5 h / 23 °C

2.1: 96 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

3.1: 89 percent / tributyltin hydride; AIBN / benzene / 8 h / 80 °C

4.1: H₂ / Pd/C / ethanol / 18 h / 23 °C / 760 Torr

5.1: 2.68 g / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 23 °C

6.1: trimethylsilyl chloride / tetrahydrofuran / 5 h / -78 °C

6.2: 95 percent / H₂ / Pd/C / ethanol / 12 h / 23 °C / 760 Torr

7.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 23 °C

8.1: 92 percent / KF; KHCO₃; hydrogen peroxide / tetrahydrofuran; methanol; H₂O / 24 h / 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; potassium fluoride; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hydrogencarbonate; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 5.1: Dess-Martin oxidation / 6.1: Grignard addition / 8.1: Tamao-Fleming oxidation;

DOI:10.1021/ol0508734

upstream raw materials:

methyl (R)-2-(N-(4-methoxybenzyl)acrylamido)-2-((benzyloxy)methyl)-3-oxybutanoate

Downstream raw materials:

methyl (2R,3S)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde

(2S,3S,4R)-2-Formyl-1-(4-methoxy-benzyl)-3,4-dimethyl-5-oxo-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid methyl ester

(3R,3aS,7aR)-3-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

(2R,3S,4R)-2-Hydroxymethyl-1-(4-methoxy-benzyl)-3,4-dimethyl-5-oxo-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid methyl ester